Invest Like The Best

This coming weekend is the annual Berkshire Hathaway shareholder meeting in Omaha. That means this week is the perfect opportunity to discuss a topic which will likely figure prominently at Berkshire this weekend: Ted Seides’s famous bet with Buffett. Ted and I discuss the origins of the bet, the nuances beneath the headlines, and whether he’d make the bet again for the next ten years. Along the way, we cover many hot topics like hedge funds, alternatives, fees, and indexing. Please enjoy! For comprehensive show notes on this episode go to http://investorfieldguide.com/bet For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Danny Moses, who was directly in the middle of the biggest trades in market history, chronicled by Michael Lewis in his book the Big Short. Danny was the head trader on the Frontpoint team led by Steve Eisman, which was one of a small group of firms that figured out, in real time, the dire situation with mortgage-backed securities during the financial crisis, and how to build a portfolio to bet against the U.S. housing market. We cover his part in the Big Short story, but also lots of other interesting ground, including the state of sell-side research and financial markets. I love conversations with traders because they live and breathe market risk. You’ll be able to see why quickly in this great conversation with Danny Moses.   For comprehensive show notes on this episode go to http://investorfieldguide.com/danny For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at Inves

In this episode, I continue to pull on one of the most interesting threads that I have uncovered while producing this podcast: the world of permanent equity. My guests today are Royce Yudkoff and Rick Ruback, two Harvard Business School professors who have partnered to create a popular class that teaches students how to search for, acquire, and run a small business directly after graduation. I approach this conversation from an investors standpoint. LP investors usually partner with these searchers to form what is called a search fund. A search fund allows recent MBA grads to spend time looking for a business and ultimately acquire it. The result is a small scale but often high return proposition for investors. I loved our discussion of what to look for in a business and what to avoid. The principles we list are useful for investors of any kind, and will particularly appeal to those from the buy and hold, value investing, and quality investing camps. One point of note which wasn’t captured during the record

SPECIAL EPISODE: Introducing Capital Allocators Podcast with Host Ted Seides This is a special episode to premiere a new podcast from my friend, Ted Seides. In this show, Capital Allocators, Ted will feature a broad range of people that control the flow of money through the capital markets.  Ted is in a unique position to this; he knows this world as well as anyone having spent with both allocators and the money managers who invest on their behalf.  Below is the information about this first episode including a link to the homepage of this show, where you can subscribe.   Enjoy the first full episode of Capital Allocators. ———————————————————————— Steven Galbraith is best known as the former Chief Investment Strategist at Morgan Stanley. He also sat in every seat in the asset management industry – credit and equity analyst, portfolio manager, business executive, entrepreneur, and Board member at an endowment and a large family office. We discuss Steve's journey, incorporating his deep insights in the inves

This week’s episode is the most unique to date. My guest is Boyd Varty, who grew up in the South African Bush, living among and tracking wild leopards. The main theme of our conversation is tracking, and how the same strategy for pursuing animals in the wild can be applied to all aspects of our lives. Boyd’s family has been tracking animals for four generations, and he is bringing what they have learned to a larger audience around the world.   The episode includes the best answer I’ve ever heard (which comes when I ask Boyd to describe his most memorable experience). We also discuss the dangers of an achievement or goal oriented mindset, and what he learned from spending time with Nelson Mandela as a boy.   This episode is one I hope you share with those you love, because I think Boyd’s ideas will have a profound impact on many who are thinking about what to do with their lives—whether they are young or old.   Please enjoy.   For comprehensive show notes on this episode go to http://investorfieldguide

My guest this week is Khe Hy. Khe has a very interesting, two-part story. We start with Khe's career at Blackrock, where he rose to be one of the youngest MDs at the firm, specializing in quantitative hedge funds. Khe shares his perspective on how the hedge fund landscape has changed and what investors should look for in hedge fund managers in the future.   The second part of the story is about Khe's attempt to understand himself. We get into fear, joy, and all that he has learned across several years of introspection and exploration. His lessons coalesce around four key pillars--compassion, stillness, uncomfortable introspection, and finding truth. We explore what he means by each of these ideas in detail. I don’t think that Khe is capable of lying. He is one of the most honest people I've met, for better or worse, and was kind to share both his struggles and moments of clarity on investing and life.   With Deep questions about purpose and deep questions about how to evaluate a quant hedge fund, This was

This week, my good friends Ted Seides and Brent Beshore join me to discuss the future of asset management and a ton of fun side topics. While we are all passionate about investing, we’ve had very different careers: Ted in alternatives, hedge funds and fund of funds, Brent in lower middle market private equity, and my own in quantitative equities. What we share is a passion for investing in general, and a deep interest in where the asset management business and profession is going.   This conversation starts like most episodes—a somewhat structured exploration of the investing business –but morphs to be a bit more fun and informal as we work our way through a bottle or two of wine. In the later half, we talk about how to dissect an industry, common features of good businesses within a given industry, books we’d like to write, books we wish existed, and things we’ve learned in our careers.   For comprehensive show notes on this episode go to http://investorfieldguide.com/brentandted For more episodes go to

My guest this week is my father, Jim O’Shaughnessy. He was a pioneer in quantitative equity research, part of an early group of explorers who combed through data to find factors which predicted future stock returns. While we’ve both written extensively on factor investing, we chose to mostly avoid that topic for this conversation. Instead, we discuss what has been a fascinating and colorful career on Wall Street. We talk about the power of premeditation, formative books, and his crazy experience during the dot-com boom when he ran a robo-advisor 15-years ahead of its time.   For comprehensive show notes on this episode go to http://investorfieldguide.com/jim For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guests this week are Trish and James Higgins, who run Chenmark Capital Management.  In this episode we continue to explore a style of investing I call Permanent Equity.  Returns in permanent equity come first from the ongoing cash flows of portfolio companies, not from reselling businesses down the line.  The partners are Chenmark are pioneering this style of small business investing and share their experience with us thus far.   For comprehensive show notes on this episode go to http://investorfieldguide.com/chenmark For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Peter Attia, M.D., whose mission is to understand and improve human lifespan and healthspan (or quality of life).  Reading Peter’s research, you find that there are many similarities between health and investing—ideas like compounding—which we explore in detail. We spend a lot of time on mind, body, spirit and performance as it relates to living a better life. Of particular interest is the strategic problem that we face when studying longevity. As Peter puts it in our conversation: we are the species of interest, but we can’t conduct the kinds of experiments on humans—randomized trials, with control groups—that we apply to solve other big problems. So we have to back our way into a better understanding of longevity and quality of life. To that end, we discuss what we can learn from studying centenarians, the problem of progress in science, a drug called Rapamycin (which Peter believes could be revolutionary), eating, the importance of muscle mass, and the idea of distressed tolerance. 

My guest this week is John Rogers, founder, CEO and CIO of Ariel investments, one of the longest standing asset management businesses still in existence.  John has a very impressive resume.  In addition to his success at Ariel, he was the captain of the Princeton University men’s basketball team, he was the co-chair of Barack Obama’s Presidential Inauguration, he sits on the board of McDonald’s, and he has given back to his community more than I can list here.  John and I discuss Ariel’s investment process and its evolution over the years, lessons from John’s basketball career, value investing, and asset management’s diversity problem among many other interesting issues. Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/rogers/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_osh

My guest this week is Alex Moazed, the co-author of Modern Monopolies: What It Takes to Dominate the 21st Century Economy, which explores the platform business model (Uber, Airbnb, Github).  Alex is also the founder and CEO of Applico, a company that he started in his dorm room that is since grown into a huge enterprise that helps startups and Fortune 500 innovate with platforms.  Alex and I talk about history and future of businesses and different types of business models.  There’s a lot in here for investors, entrepreneurs, and historians.  Please enjoy!   For comprehensive show notes on this episode go to http://investorfieldguide.com/alex/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Ian Cassel, a microcap investor who is always on the lookout for small companies which are run by men and women who are what he calls intelligent fanatics. Ian’s livelihood is based on the success or failure of a small group of companies that you have never heard of—he takes the idea of “skin in the game” to another level. We explore what Ian looks for in managers, why investors might want to invest in microcap companies, and the benefits of a frugal approach to life. Buying public companies that are as small as the ones which Ian considers is an entirely different style of investing than what most of us are used to in the public markets. Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/ian/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag  

My guest this week is Joe Mansueto, the founder, longtime CEO and current executive chairman of Morningstar, Inc.  Joe is an entrepreneur at heart. He has the gene for spotting good business ideas and building them out with the customer in mind, so it is no surprise that the story behind Morningstar’s birth and growth is both entertaining and enlightening. While there are many business lessons in this episode, there is just as much to be learned from the way Joe conducts himself. He was kind, welcoming, and humble—you’ll see what I mean. There is something timeless and classic about his journey—I hope you enjoy hearing about it as much as I did.   For comprehensive show notes on this episode go to investorfieldguide.com/joe/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag  

Brent Beshore and I spoke for 10 hours about all things investing and business, and decided to record a 2-hour chunk of our conversation. We start by discussing private equity, venture capital, and the importance of brand. We then explore the difference between public and private company valuation, and the potent idea of peer mentorship.  The conversation wraps up with Brent’s recent experience with one of the greatest investors and thinkers of all time.  Above all, this is a conversation about what is right and wrong in the world of money management and investing, and where the business is heading.  Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/adventures/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is writer, director, producer, and podcast host Brian Koppelman, who’s film credits include ‘Rounders’, ‘Oceans 13’, and ‘Solitary Man’. More recently he co-created the Showtime show, ‘Billions’, which allowed us to have some fun talking about the world of hedge funds and investing.  Brian’s method for chasing curiosity is something that everyone can learn apply in their own lives.  In this chat, we discuss creativity, the importance of storytelling and why we are all so intrigued by billionaires.  Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/koppelman/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

Jeremiah Lowin is probably the smartest guy I know, and that is saying something. He is an expert in the fields of statistics, artificial intelligence, and risk management—among many other things.  He is currently the Director of Risk Management for a private investment firm in the New York area, but has spent years working with machine learning and AI.  This conversation is broken up into two parts.  In the first part, we explore artificial intelligence, machine learning, and models.  Then we shift to what risk means in a portfolio and how it can be managed or at least redistributed (which starts around 40 minutes into the conversation).  Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/lowin/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

This week’s episode features the partners of the Collaborative Fund, a venture-capital firm based in New York City.  This is a unique, group interview with Lauren Loktev, Kanyi Maqubela, and Craig Shapiro that explores all aspects of their search and investing process, including how they identify thematic change in the world and then build a portfolio around those themes.  The quality of a team is crucial to success in investing and this is a great example of a team with chemistry on a singular mission.  They all offer great advice on how to operate a business, build a team, and find interesting new investments.    Also, stay tuned to the end for a bonus segment captured while the tape was still rolling.   Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/collaborative/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/book

My guest today is Dan Egan, who is the managing director of Behavioral Finance and Investing at Betterment.  In this wide-ranging role, Dan has his hands is most of the ways that Betterment interacts with its clients and how it invests their money. This is one very interested and smart guy who is clearly passionate about helping investors make better decisions.  In this conversation, we explore everything from science fiction, automation, investor behavior and how Betterment tries to solve problems that goes beyond the automated asset allocation that is their bread and butter.   Please enjoy.   For comprehensive show notes on this episode go to investorfieldguide.com/egan/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Shane Parrish, who created the extremely popular Farnam Street—a website dedicated to understanding the world by mastering the best of what others have already figured out.  More than 100,000 people subscribe to the Farnam Street Newsletter which summarizes what Shane and his team learned and wrote that week. I read it every Sunday. Shane and I cover a lot of ground including the future of work, automation, mental models, and reading.  Shane is a voracious reader and offers unique suggestions for finding your next great book.   Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/parrish/ For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag